194-69-4Relevant articles and documents
Methylarene-based PAH synthesis via domino cyclization of 1, 1-difluoro-1-alkenes
Fuchibe, Kohei,Takao, Go,Takahashi, Hiroki,Ijima, Shiori,Ichikawa, Junji
, p. 2019 - 2029 (2019/12/23)
Polycyclic aromatic hydrocarbons (PAHs) containing 4-7 benzene rings were synthesized via a methylarene-based protocol. Trimethyl[2-(trifluoromethyl)allyl]silane was electrophilically benzylated with Ar1CH2Br (prepared from Ar1CH3) to afford 2-trifluoromethyl-1-alkenes that were in turn nucleophilically benzylated with Ar2CH2Li (prepared from Ar2CH3) through an SN2-type reaction to produce 1, 1-difluoroethylenes, which are cyclization precursors bearing two 2-arylethyl groups. Magic acid efficiently promoted the domino FriedelCrafts-type cyclization of these precursors, followed by dehydrogenation that enabled the connection among two aryl groups (Ar1 and Ar2) by forming two benzene rings between them, facilitating the synthesis of the desired higher-order PAHs. With the proposed protocol, the combination of even a limited number of methylarenes can yield a variety of PAHs in diverse configurations.
A convenient and general synthesis of cata- and peri-condensed polycyclic aromatic hydrocarbons with a Fjord-region
Kumar, Subodh
, p. 841 - 844 (2007/10/03)
Cata- and peri-condensed polycyclic aromatic hydrocarbons (PAHs) 10a-d and 11 have been conveniently synthesized by the application of Suzuki cross-coupling reaction. In three to four steps, these PAHs having fjord-region were obtained in an overall yield of 35-51% from commercially or easily accessible aryl boronic acids and aryl bromides.
Photochemistry of Electron-Rich 1,3-Distyrylbenzenes
Noller, Klaus,Kosteyn, Frank,Meier, Herbert
, p. 1609 - 1616 (2007/10/02)
The 1,3-distyrylbenzenes 3, containing up to seven alkoxy groups, are subjected to the oxidative photocyclization.Elimination of methanol (3bb -> 7bb, 3bf -> 7bf) and quinone oxidation can occur as competitive or consecutive reactions in the formation of the products 6, 7, and 8.Selfsensitized generation of singlet oxygen by 6bf can lead to endoperoxide formation (6bf -> 11).